Chloroacetonitrile → HCID 23350111, compound

HRID 2058272Notes

Reaction equation

HRID 2058272 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.Cl[CH2:19][C:20]#[N:21]>CN(C)C=O.O>[Cl:3][C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:19][C:20]#[N:21])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 123461204-(4-Chlorophenoxy)phenol

Product 1

HCID 23350111HCID 23350111, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

10.88 g of a 50% sodium hydride suspension in mineral oil are diluted with 230 ml of absolute dimethylformamide and treated within 30 minutes with a solution of 50 g of p-(p-chlorophenoxy)phenol in 230 ml of absolute dimethylformamide while the temperature rises slightly. The mixture is then stirred at room temperature for 30 minutes. A solution of 18.8 g of chloroacetonitrile in 200 ml of absolute dimethylformamide is added dropwise while cooling the mixture in a water-bath. The mixture is stirred at 50° C. overnight, then cooled and diluted with 1 liter of water. This mixture is extracted five times with 200 ml of ethyl acetate each time. The organic phases are washed twice with 100 ml of 2-N sodium carbonate solution, once with 100 ml of saturated sodium chloride solution and then dried over magnesium sulfate and evaporated. The crude product (80 g of a dark oil) is purified by chromatography on silica gel using toluene for the elution to yield 45 g of [p-(p-chlorophenoxy)phenoxy]acetonitrile (76%) as a colorless oil.

Workup

  1. temperaturewhile cooling the mixture in a water-bath
  2. stirringThe mixture is stirred at 50° C. overnight
  3. temperaturecooled
  4. extractionThis mixture is extracted five times with 200 ml of ethyl acetate each time
  5. washThe organic phases are washed twice with 100 ml of 2-N sodium carbonate solution, once with 100 ml of saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe crude product (80 g of a dark oil) is purified by chromatography on silica gel
  9. washfor the elution

Sources & evidence

ORD record
ord-07b1ca697a464321a9bb77466f00c693
Source dataset
uspto-grants-1980_07
Patent number
US04215139

Reaction notes

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